Trimethyl orthoformate → (2-Methoxy-1,3-dioxan-5-yl)methanol

HRID 31592

Reaktionsgleichung

Reaktionsgleichung von HRID 31592
[OH:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[CH:8](OC)(OC)[O:9][CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[CH3:8][O:9][CH:10]1[O:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2][O:1]1

Komponenten

5

Edukt 3

HCID 9005Trimethyl orthoformateHCID 78432TrimethylolmethaneHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 59792360(2-Methoxy-1,3-dioxan-5-yl)methanolAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2-(hydroxymethyl)-1,3-propanediol (1.7 g, 16 mmol), trimethyl orthoformate (7 ml, 64.1 mmol), and p-toluenesulfonic acid monohydrate (275 mg, 1.6 mmol) was stirred at room temperature for 22 hours. To the reaction mixture, triethylamine (447 μl) was added and the mixture was concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (1.4 g, 59.1% yield), which is a cis and trans (1:1) mixture, as a light yellow oil.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-900281ff6a674c459015a992c92073ad
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

Verknüpfte Notizen

Wird geladen…